CA2382129C - Nouveaux derives de flavones, de xanthones et de coumarines - Google Patents
Nouveaux derives de flavones, de xanthones et de coumarines Download PDFInfo
- Publication number
- CA2382129C CA2382129C CA2382129A CA2382129A CA2382129C CA 2382129 C CA2382129 C CA 2382129C CA 2382129 A CA2382129 A CA 2382129A CA 2382129 A CA2382129 A CA 2382129A CA 2382129 C CA2382129 C CA 2382129C
- Authority
- CA
- Canada
- Prior art keywords
- group
- substituted
- ring
- ring atoms
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
L'invention concerne des nouveaux composés représentés par la formule (I): Z-OCH¿2?-C.ident.CCH¿2?NRR?1¿, ou un sel ou un solvate pharmaceutiquement acceptable, dans laquelle Z peut représenter les formules (IA) ou (IB). Les composés présentent une activité antiproliférative et sont utilisés comme modulateurs de la résistance multidrogue dans une chimiothérapie contre le cancer. Les composés peuvent également être utilisés pour la fabrication d'un médicament destiné au traitement ou à la prévention de tumeurs et de troubles de la ménopause et de l'ostéoporose.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9920912.4A GB9920912D0 (en) | 1999-09-03 | 1999-09-03 | Novel derivatives of flavones,xanthones and coumarins |
GB9920912.4 | 1999-09-03 | ||
PCT/EP2000/008365 WO2001017985A1 (fr) | 1999-09-03 | 2000-08-28 | Nouveaux derives de flavones, de xanthones et de coumarines |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2382129A1 CA2382129A1 (fr) | 2001-03-15 |
CA2382129C true CA2382129C (fr) | 2010-07-06 |
Family
ID=10860348
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2382129A Expired - Fee Related CA2382129C (fr) | 1999-09-03 | 2000-08-28 | Nouveaux derives de flavones, de xanthones et de coumarines |
Country Status (21)
Country | Link |
---|---|
US (1) | US6608089B2 (fr) |
EP (1) | EP1212312B1 (fr) |
JP (1) | JP4782337B2 (fr) |
KR (1) | KR100819575B1 (fr) |
CN (1) | CN1229370C (fr) |
AT (1) | ATE236147T1 (fr) |
AU (1) | AU775790B2 (fr) |
CA (1) | CA2382129C (fr) |
CZ (1) | CZ300939B6 (fr) |
DE (1) | DE60001974T2 (fr) |
DK (1) | DK1212312T3 (fr) |
ES (1) | ES2195933T3 (fr) |
GB (1) | GB9920912D0 (fr) |
HK (1) | HK1043368A1 (fr) |
HU (1) | HUP0202578A3 (fr) |
NO (1) | NO327911B1 (fr) |
PL (1) | PL211887B1 (fr) |
PT (1) | PT1212312E (fr) |
RU (1) | RU2252221C2 (fr) |
SK (1) | SK286402B6 (fr) |
WO (1) | WO2001017985A1 (fr) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2001288432A1 (en) | 2000-09-01 | 2002-03-22 | Icos Corporation | Materials and methods to potentiate cancer treatment |
PL205635B1 (pl) * | 2001-04-09 | 2010-05-31 | Inst Farmaceutyczny | Nowe pochodne genisteiny i zawierające je środki farmaceutyczne |
CN100381437C (zh) | 2002-04-17 | 2008-04-16 | 赛特凯恩蒂克公司 | 化合物、组合物和方法 |
JP2005533119A (ja) | 2002-07-17 | 2005-11-04 | サイトキネティクス・インコーポレーテッド | 化合物、組成物、及び方法 |
US7105542B2 (en) * | 2002-08-02 | 2006-09-12 | The Ohio State University Research Foundation | 2-Heterosubstituted 3-aryl-4H-1-benzopyran-4-ones as novel therapeutics in breast cancer |
JP2005539062A (ja) * | 2002-09-13 | 2005-12-22 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
CA2515135A1 (fr) * | 2003-02-04 | 2004-08-19 | Kabushiki Kaisha Yakult Honsha | Inhibiteur de la proteine resistant au cancer du sein |
CA2523178C (fr) | 2003-03-24 | 2012-10-23 | Luitpold Pharmaceuticals, Inc. | Materiaux et procedes de potentialisation d'un traitement anticancereux |
US20050165089A1 (en) * | 2003-10-06 | 2005-07-28 | Gustave Bergnes | Compounds, compositions and methods |
GB0412768D0 (en) * | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
GB0412769D0 (en) | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
FR2929276B1 (fr) * | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
CN101497593B (zh) * | 2009-03-18 | 2011-09-21 | 华南理工大学 | 5-羟基香豆素和吡喃型香豆素类化合物及合成方法与应用 |
CN102946881A (zh) * | 2010-04-23 | 2013-02-27 | 奇尼塔公司 | 抗病毒化合物 |
CN101985449B (zh) * | 2010-09-28 | 2012-08-22 | 中山大学 | 一种香豆素衍生物及其制备方法和作为抗癌药物的用途 |
CN103113340B (zh) * | 2013-01-21 | 2015-08-19 | 四川大学 | 一类金雀异黄酮烷基胺类化合物、其制备方法和用途 |
CN103232462B (zh) * | 2013-05-13 | 2016-03-02 | 湖北科技学院 | 香豆素-吡咯类化合物的合成方法 |
CN103408554B (zh) * | 2013-07-31 | 2015-07-08 | 西安交通大学 | 一种具有降高血压活性的吡咯香豆素类化合物及制备方法 |
CN104274455B (zh) * | 2014-09-24 | 2018-04-27 | 山东理工大学 | 含苄基哌嗪槲皮素衍生物制法及其对胃黏膜保护作用 |
CN107641109B (zh) * | 2017-10-16 | 2019-05-24 | 厦门大学 | 一种类黄酮化合物及其制备方法和应用 |
CN107602520B (zh) * | 2017-10-16 | 2019-06-14 | 厦门大学 | 一种含哌嗪环的类异黄酮化合物及其制备方法和应用 |
KR102109151B1 (ko) | 2018-06-28 | 2020-05-11 | 영남대학교 산학협력단 | 잔톤 유도체의 신규한 제조방법, 이로 제조된 신규한 잔톤 유도체 및 이들을 포함하는 조성물 |
CN110156735B (zh) * | 2019-04-23 | 2023-05-12 | 天津国际生物医药联合研究院 | 芒柄花黄素衍生物及其制备方法和应用 |
CN110240579B (zh) * | 2019-06-10 | 2023-03-31 | 中国科学院成都有机化学有限公司 | 一种多取代γ-丁内酯类化合物、制备方法及其应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513198A (en) * | 1965-10-22 | 1970-05-19 | Hoffmann La Roche | Aryloxy- and arylthio-acetylenic amines and the salts thereof |
FR2378519B1 (fr) * | 1976-11-24 | 1982-08-06 | Unicler | |
JPH03163017A (ja) * | 1989-08-24 | 1991-07-15 | Nisshin Flour Milling Co Ltd | 抗癌活性増強剤 |
US5399561A (en) | 1989-09-19 | 1995-03-21 | Allergan, Inc. | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydro-quinolinyl group having retinoid-like biological activity |
US5023341A (en) * | 1989-09-19 | 1991-06-11 | Allergan, Inc. | Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
JP2514500B2 (ja) * | 1991-09-14 | 1996-07-10 | 呉羽化学工業株式会社 | 多剤耐性抑制剤及び発現阻害剤 |
EP0649410B1 (fr) * | 1992-07-10 | 1997-05-02 | Laboratoires Glaxo Sa | Derives d'anilide |
US5852033A (en) * | 1995-06-29 | 1998-12-22 | Pharma Mar, S.A. | Methods of treatment using lamellarin-class alkaloids |
JPH1036260A (ja) * | 1996-07-18 | 1998-02-10 | Mitsui Norin Kk | 抗ガン剤の効力増強方法 |
-
1999
- 1999-09-03 GB GBGB9920912.4A patent/GB9920912D0/en not_active Ceased
-
2000
- 2000-08-28 JP JP2001521732A patent/JP4782337B2/ja not_active Expired - Fee Related
- 2000-08-28 EP EP00958505A patent/EP1212312B1/fr not_active Expired - Lifetime
- 2000-08-28 KR KR1020027002800A patent/KR100819575B1/ko not_active IP Right Cessation
- 2000-08-28 PL PL356699A patent/PL211887B1/pl not_active IP Right Cessation
- 2000-08-28 SK SK309-2002A patent/SK286402B6/sk not_active IP Right Cessation
- 2000-08-28 DK DK00958505T patent/DK1212312T3/da active
- 2000-08-28 CZ CZ20020785A patent/CZ300939B6/cs not_active IP Right Cessation
- 2000-08-28 ES ES00958505T patent/ES2195933T3/es not_active Expired - Lifetime
- 2000-08-28 DE DE60001974T patent/DE60001974T2/de not_active Expired - Lifetime
- 2000-08-28 CN CNB008121818A patent/CN1229370C/zh not_active Expired - Fee Related
- 2000-08-28 PT PT00958505T patent/PT1212312E/pt unknown
- 2000-08-28 RU RU2002108565/04A patent/RU2252221C2/ru not_active IP Right Cessation
- 2000-08-28 AU AU70000/00A patent/AU775790B2/en not_active Ceased
- 2000-08-28 CA CA2382129A patent/CA2382129C/fr not_active Expired - Fee Related
- 2000-08-28 WO PCT/EP2000/008365 patent/WO2001017985A1/fr active IP Right Grant
- 2000-08-28 HU HU0202578A patent/HUP0202578A3/hu unknown
- 2000-08-28 AT AT00958505T patent/ATE236147T1/de active
-
2002
- 2002-02-15 US US10/075,628 patent/US6608089B2/en not_active Expired - Fee Related
- 2002-03-01 NO NO20021050A patent/NO327911B1/no not_active IP Right Cessation
- 2002-07-09 HK HK02105077A patent/HK1043368A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE60001974T2 (de) | 2004-02-19 |
NO20021050L (no) | 2002-05-03 |
GB9920912D0 (en) | 1999-11-10 |
KR100819575B1 (ko) | 2008-04-04 |
CZ2002785A3 (cs) | 2002-06-12 |
NO20021050D0 (no) | 2002-03-01 |
DK1212312T3 (da) | 2003-07-21 |
CA2382129A1 (fr) | 2001-03-15 |
AU7000000A (en) | 2001-04-10 |
CN1229370C (zh) | 2005-11-30 |
PL211887B1 (pl) | 2012-07-31 |
PT1212312E (pt) | 2003-08-29 |
JP2003508524A (ja) | 2003-03-04 |
RU2252221C2 (ru) | 2005-05-20 |
US6608089B2 (en) | 2003-08-19 |
SK286402B6 (sk) | 2008-09-05 |
WO2001017985A1 (fr) | 2001-03-15 |
JP4782337B2 (ja) | 2011-09-28 |
CN1371371A (zh) | 2002-09-25 |
PL356699A1 (en) | 2004-06-28 |
CZ300939B6 (cs) | 2009-09-16 |
DE60001974D1 (de) | 2003-05-08 |
EP1212312A1 (fr) | 2002-06-12 |
ES2195933T3 (es) | 2003-12-16 |
HK1043368A1 (en) | 2002-09-13 |
SK3092002A3 (en) | 2003-10-07 |
HUP0202578A2 (hu) | 2002-11-28 |
KR20020030801A (ko) | 2002-04-25 |
HUP0202578A3 (en) | 2005-02-28 |
US20020183318A1 (en) | 2002-12-05 |
AU775790B2 (en) | 2004-08-12 |
EP1212312B1 (fr) | 2003-04-02 |
NO327911B1 (no) | 2009-10-19 |
ATE236147T1 (de) | 2003-04-15 |
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Date | Code | Title | Description |
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EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20140828 |